Football pools are not contests of football knowledge or predictive ability: they’re contests of strategy and discipline.

Strategy paradox: Never pick upsets for a season prize; always pick upsets for weekly prizes

For a season payout pool you stand a better chance of winning the prize if you pick all the favorites each week, regardless of whether you believe they’ll actually win. You don’t realize how overconfident you are in your own beliefs, but if you ignore them and follow the discipline you’ll be in the running entering the final week(s) of the season.

For a weekly payout pool you’ll win more often if every week you selectively pick an upset or two, even if you’re certain those underdogs won’t win. “Selectively” does not refer to using a better upset prediction model, it refers to picking teams your friends are not picking.

Discipline: On weeks when it doesn’t win the weekly payout strategy can make you look like you know nothing about football

Let’s say you’re in a 17 person pool with a weekly payout. An average participant should expect to win one payout in a 17 week season. By using the weekly strategy, you could win 2 or 3 times in a season, but you might come in dead last a dozen times too. Even though there’s no cost to losing badly versus losing well, not winning several weeks in a row can undermine your confidence in the strategy